Salts of phenyl esters of trialkyl ammoniumethanesulfonic acids



United States Patent 3,171,852 SALTS 0F PHENYL ESTERS 0F TRIALKYL AMMONIUMETHANESULFONIC ACIDS Harry Distler, Gerhard Leibner, and Ernst-Heinrich Pommer, Ludwigshafen (Rhine), and Herbert Stummeyer, Mannheim, Germany, assignors to Badische Anilin- & Soda-Fabrik Aktiengesellsehaft, Ludwigshafen (Rhine), Germany No Drawing. Filed July 30, 1962, Ser. No. 213,161 Claims priority, application Germany, Sept. 6, 1961, B 63 913 3,171,852 Patented Mar. 2, 1955 Where Ar, R R R and Y have the meanings given above.

The preparation of a compound to be employed according to the invention is described in the following. Other compounds can be obtained in an analogous way. The parts specified are parts by Weight.

1 Claim. (Cl. 260456) 126 parts dimethyl sulfate and 500 parts benzene are This invention relates to new fungicidal compounds Into 229 P of h P y ester of y fl and a Process of controlling fungi therewith amlnoethanesulfomc acid and 500 parts benzene with It has been found that compounds of the formula P P at a temhefahlfe of 20 C- to 40 C. A reduc- R1 69 tron 111 the evolutlon of heat indicates that the exothermic 9 reaction is complete. AI OSO2' CXI ?XYIII*RZ Y The substance which precipitates from the benzene H H R; solution is separated off and washed with 1000 parts benin which Ar is an aromatic radical which may besub- After fy 312 P of h P y ester of tit t d b one or more h l atoms, lk l it b tr1n1ethyl-/3-ammoethanesulfomc acld methyl sulfate is droxyl, acyl, formyl, ethoxy, methoxy, nitrile, acylamino Ohtfllhed- This 18 a yield of 873% of the y- The or thiocyanate groups, X i hydrogen, an lk l di l or substance melts at 129 C. and has the following formula: halogen and X is hydrogen, an alkyl radical or halogen, 6 R R and R are alkyl radicals and Y is an anion, such 3 3 as halogen, I", Br-, Cl, CH OSO CH =CHSO V acetate or sulfate, have an excellent fungicidal action. funglcldes Fccordmg to the 1nVePt1n are obtalned The compounds are particularly suitable for treating seeds by mlxmg the acme subs tan ces,wlth f h or camefs, or plants before planting. They are also suitable for the Such as water and Orgamc E dlspersmg Wettmg control of fungi in the earth, for example, by moistening agents, solid substances or mixtures thereof. The adthe earth with an aqueous Solution of the compound The mixture of other active substances, such as those with nature of the anion has no Significant influence on the acarici d al, insecticidal, ov cidal, herbicidal, fungicidal or fungicidal effect and the anion may be selected as desired. PactenFldal W pos slble- The substances decribed The compounds are also suitable for the control of fungi m lnventlon apphed by the usual methods by in cooling Water systems and on leather. treat ng the ob ects or plants to be protected against The compounds are readily obtainable by reacting esters funglcldal attack wlth a fungltoxlc afnmmt active of aromatic hydroxyl compounds of a,fi-olefinically un- Stance To f fungus gmWth Saturated sulfonic vacids (see pending Us patent app1ica terns, a fungitoxlc amount of active substance is dissolved tion Serial 43,009, filed July 15, 1960, by Harry in the cooling water. The new substances are miscible Distler) with secondary amines followed by alkylation to With Water all proportions. yield a quaternary ammonium salt according to the 40 Thefollowmg examples illustrate the application of the lowing equation: funglcldes' R1 EXAMPLE 1 AI OSO2 CH=CH2 Mixtures of parts active substance and 35 parts talc are finely ground. 2 g. of these mixtures are applied uni- Rfi R 45 formly to 1 kg. of seed peas of the variety Senator. I peas are then planted in seed boxes in strongly infected ArOSOzOH2CHiN\ a compost. The peas which have germinated after 7 and 14 days are counted.

TABLE Number of peas germinated after- Substance 7 Days 14 Days 69 9 [Q0SO2CH2CH2N(CH3)3]QH3OSO3 s3 84 G9 9 [@osmomcm-monm]om=on-soz s3 s2 Comparative substance ,3 EXAMPLE 2 The active substances are added in varying quantities down to 1 ppm. to a nutrient solution which provides optimum conditions for the growth of the fungus Aspergillus niger. 20-ml. portions of the nutrient solutions treated in this way and contained in 100 m1. Erlenmeyer flasks are inoculated with 0.3 mg. Aspergillus spores. The flasks are maintained for 120' hours at 36 C. and the degree of fungus growth, which takes place preferentially at the surface'of the nutrient solution, is assessed; The results are asgiven in thetable below in which 0 indicates nofungus growth, while 5 indicates uninhibited fungus growth, the fungus completely covering the surface of r the nutrient solution.

, We. claim: Compounds of the formula in which Ar is a member selected from the group'consisb ing of phenyhphenyl substituted by chlorine, and phenyl substituted by methyl, R R and R are lower alkyl radicals and Y is an anion.

Fungicide Quantity of Fungicide in the nutrient solution in p.p.m.

ea 6 OSO CHzCHgN(GH3);; I CH OSO o o 2 3 5 5 G9 '9 -OSOzCHg-CHz-N(OH3)3 CH3OSO3 o o 0 1 3 5 ea 7 6 01 -oso2oH2cH2N onmjomoso, 0 0 0 2 3 5 6B '9 Cl -OSOzCHz-CH2N(CH:4)3 CHaOS03 0 O O 2 3 5 6B 6 OSOzOHzCHzN(CHa)s CH;0S03 o o 0 3 3 5 6B 6 c1- -OSO2-CEz-C 2N(CHs)s C[aOS03 0 0 0 3 4 5 01 OS'Or-OH CH2 N(CH /'TCH OSO3 0 0 3 5 3 5 e e 7 c1 OSOz-CH CH2-N(CH CHaOSO3 0 0 0 4 s 3 Control (untreated); 3 5 5 3 5 5 References Cited in the file of this patent UNITED' STATES PATENTS OTHER 'REFEREN CES Nerdel et a1. Ber. Deut Chem., vol. 92, pp. 2460- 

